Ethyl Bromide → Methyl 9-ethylxanthene-9-carboxylate

HRID 750550

Reaction equation

HRID 750550 reaction equation
[CH:1]1[C:14]2[CH:13]([C:15]([O:17][CH3:18])=[O:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:19][C:20](C)([O-])C.[K+].BrCC>O1CCCC1>[CH2:19]([C:13]1([C:15]([O:17][CH3:18])=[O:16])[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[O:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:20]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 699662methyl 9H-xanthene-9-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 68962313Methyl 9-ethylxanthene-9-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.0 g (0.042 mol) of methyl 9-xanthenecarboxylate (obtainable according to step 1.1.a) are dissolved in 100 mL of tetrahydrofuran and combined batchwise with 5.16 g (0.044 mol) of potassium tert-butoxide while cooling. Then at about 18° C. to 22° C., 6.296 mL (0.083 mol) of bromoethane are added dropwise; after it has all been added, the mixture is stirred for about 1.5 hours at ambient temperature. The precipitate formed is suction filtered and the solvent is removed by distillation. The residue remaining is taken up in diethyl ether and extracted with water. The organic phase is dried over magnesium sulfate and the solvent is removed by distillation. The crude product obtained is used in the next step without any further purification. Yield: 7.92 g of yellow oil (70% of theoretical yield).

Workup

  1. temperaturewhile cooling
  2. additionall been added
  3. customThe precipitate formed
  4. filtrationfiltered
  5. customthe solvent is removed by distillation
  6. extractionextracted with water
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. customthe solvent is removed by distillation

Sources & evidence

ORD record
ord-d4816aa31f8c4b9b84fc990dd7d05bb4
Source dataset
uspto-grants-2008_07
Patent number
US07405224B2

Linked notes

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